When the FBI Captured Whitey Bulger, the Idealistic Crime Family Myth Finally Died

The arrest of the notorious Boston gangster James “Whitey” Bulger would be an easy story to tell if he was the object of national hatred like you might expect a ruthless murderer to be. But to see the local reaction to his arrest last Wednesday, you would have thought they were busting a charming rogue along the lines of Bad Santa.

You have to understand Boston. Whitey Bulger is more than just another criminal here. He is the embodiment of a timeless local myth about immigration, family, and community, rooted in a time when crime made sense as a survival strategy and the perpetrators were people we recognized. That sympathetic dividend has only grown in his absence, undeserved as it may be.

Since Whitey fled Boston in 1995, Americans witnessed the most devastating attack in our nation’s history and came to a new understanding of big-time crime networks. Frank McCourt’s best-selling 1996 memoir Angela’s Ashes had already triggered a renewed fascination with all things Irish, and an unapologetic part of this Hibernian vogue was a nostalgia for gang crime that felt almost friendly – draw a pint, laddie! -- compared to the less familiar threat of global terrorism.

That nostalgia was present in the historical depictions of the Five Points neighborhood in the film Gangs of New York. But we also looked to the working-class neighborhood of South Boston, affectionately known as Southie, where Whitey Bulger was the last crime lord of a fading dynasty. It is no coincidence that the screenplay for the 2006 blockbuster The Departed was adapted by William Monahan, a Southie native, or that Jack Nicholson’s character was based firmly on Whitey Bulger. His story provided a modern fantasy, bleak though it was, in which the language of the tough tawkin mugsie was still being spoken.

“The Age of Bulger transpired during a time when most US citizens probably thought the Irish gangster no longer existed outside of black-and-white Warner Bros. movies from the 1930s,” wrote T. J. English, author of Paddy Whacked: The Untold Story of the Irish American Gangster. Whitey and the Winter Hill Gang, he said, “appeared to be caught in a time warp.”

Bulger’s image as a community figure is as important to his mystique as his brutality. He was the “neighborhood godfather,” giving turkeys to needy families on Christmas, lending money to kids, doing favors, keeping out the foreign element and settling local disputes. In Southie, the Winter Hill Gang was part of the social fabric, laying down a strict moral code (don’t rat) protecting merchants (for a price) and providing a career path (unfortunately) for impoverished youth.

But the Protector of the People was a rat himself. He oversaw the trafficking of cocaine and other drugs into Southie and was responsible for the deaths of numerous kids due to overdose and drug-related violence. At the same time, he double-crossed his associates as an informant for an FBI agent, who tipped him off to his indictment.

Whitey’s capture a decade after 9/11 is a dissonant moment with a note of tenderness. But it should also be a reality check. In Boston’s collective imagination, Bulger is the last of a breed: the thug we knew. We are living in an age where crime feels like a phantom with no respect for borders or alliances -- where terrorist threats come from foreign enemies, where faceless hackers can steal a person’s identity without ever stepping foot in the same room. With Bulger’s arrest, the legend of the neighborhood boss is over; the myth is dead. We, like Whitey, cannot run from reality.